Process for dyeing and printing cellulose fibres

ABSTRACT

For dyeing and printing cellulose fibers swollen with water-miscible swelling agents or fibre blends containing these fibres, the fibres are treated with dyestuffs of the general formula ##STR1## wherein R 1  represents aryl, 
     R 2  represents halogen, CN, CF 3 , NO 2 , Q 1 , --OQ 1 , --COOQ 1 , CONQ 1  Q 2  or --NHCOQ 1 , 
     R 3  represents H, halogen, CN, CF 3 , Q 1  or --OQ 1  and 
     K represents the radical of a coupling component, 
     wherein 
     Q 1  denotes alkyl or aryl and 
     Q 2  denotes hydrogen, alkyl or aralkyl, 
     and the dyestuffs are fixed by heat treatment.

The invention relates to a process for dyeing and printing cellulose fibres swollen with water-miscible swelling agents or fibre blends containing these fibres.

The process is characterised in that the fibres are treated with a dyestuff of the general formula ##STR2## wherein R₁ represents aryl,

R₂ represents halogen, CN, CF₃, NO₂, Q₁, --OQ₁, --COOQ₁, --CONQ₁ Q₂ or --NHCOQ₁,

R₃ represents H, halogen, CN, CFhd 3, Q₁ or --OQ₁ and

K represents the radical of a coupling component,

wherein

Q₁ denotes alkyl or aryl and

Q₂ denotes hydrogen, alkyl or aralkyl,

and the dyestuff is fixed by heat treatment.

The invention also relates to dyestuff formulations, which contain a dyestuff of the formula (I), for dyeing and printing cellulose and cellulose-containing fibre material.

The dyestuffs of the formula (I) are free from substituents which confer water-solubility. The alkyl, aralkyl and aryl radicals mentioned can contain further non-ionic substituents.

Suitable alkyl within the scope of this invention is, in particular, alkyl with 1 to 4 C atoms, which can optionally be further monosubstituted by cyano, halogen, such as chlorine, bromine or fluorine, hydroxyl or C₁ -C₄ -alkoxy, for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, tert.-butyl, cyanoethyl or 2-chloroethyl.

Suitable aryl is, in particular, phenyl which is optionally mono-, di- or tri-substituted by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, nitro, cyclohexyl or phenyl.

"Bulky" radicals are in those positions where they cause no steric hindrance, for example tert.-butyl in the m- or p-position of a phenyl radical.

Suitable halogen is chlorine, bromine or fluorine, but preferably chlorine.

Suitable aralkyl is, for example, benzyl or phenethyl.

Dyestuffs of the formula (I) wherein K represents the radical of an aniline coupling component which couples in the 4-position, the radical of an indole coupling component which couples in the 3-position or the radical of a 5-aminopyrazole coupling component which couples in the 4-position, are used in particular.

Preferred dyestuffs correspond to the formulae ##STR3## wherein R₁ ' represents phenyl, which is optionally mono-, di- or tri-substituted by C₁ -C₄ -alkyl or halogen,

R₂ ' represents halogen, CN, CF₃, NO₂, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy,

R₃ ' represents halogen, CN, CF₃, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy,

R₄ represents hydrogen, halogen, alkyl, --NHCOQ₁, --NHSO₂ Q₁, --NHCONH₂, --NHCONQ₁ Q₂, --NHCOCF₃, --NHCOOQ₁, alkoxy or --O--SO₂ --Q₁,

R₅ and R₆, which can be identical or different, represent hydrogen, C₁ -C₄ -alkyl, --C₁ -C₄ -alkylene--O--CO--Q₁, C₁ -C₄ -alkylene--O--CO--O--Q₁, C₁ -C₄ -alkylene--CO--O--Q₁, C₁ -C₄ -alkylene-CONQ₁ Q₂, C₁ -C₄ -alkylene--O--Q₁, C₁ -C₄ -alkylene--O--CO--NH--Q₁, C₁ -C₄ -alkylene--O--SO₂ --Q₁, aralkyl, --CH₂ --CH═CH₂ or --CH₂ CH₂ CN and

Q₁ and Q₂ have the abovementioned meaning. ##STR4## wherein R₇ represents C₁ -C₄ -alkyl or phenyl,

R₈ represents C₁ -C₄ -alkyl, benzyl or phenethyl,

R₉ represents hydrogen, halogen or alkyl and

R₁ ', R₂ ' and R₃ ' have the abovementioned meaning.

and ##STR5## wherein R₁₀ represents Q₂, aryl, cycloalkyl or the radical of a heterocyclic compound and

R₁₁ represents Q₁, --COOQ₂ or --CON(Q₂)₂,

and wherein

R₁ ', R₂ ', R₃ ', Q₁ and Q₂ have the abovementioned meaning.

Particularly preferred dyestuffs are those of the formulae ##STR6## wherein R₁ " represents phenyl, tolyl or chlorophenyl,

R₂ " represents halogen, nitro or cyano,

R₃ " represents halogen,

R₄ ' represents --NHCOCH₃, --NHCOC₂ H₅, --NHCOC₃ H₇, --NHCOC₄ H₉, --NHCOC₆ H₅ or --NHSO₂ CH₃, --NHSO₂ C₄ H₉ or --NHSO₂ C₆ H₅ and

R₅ ' and R₆ ', which can be identical or different, represent --C₂ H₄ --O--CO--CH₃, --C₂ H₄ --O--COC₂ H₅, --C₂ H₄ --O--CO--C₆ H₅, --C₂ H₄ --O--CO--O--CH₃, --C₂ H₄ --O--CO--O--C₂ H₅, --C₂ H₄ --O--CO--NH--CH₃, --C₂ H₄ --O--CO--NH--C₄ H₉, --C₂ H₄ --O--CO--NH--C₆ H₅ or --C₂ H₄ CN; ##STR7## wherein R₇ ' represents phenyl,

R₈ ' represents C₁ -C₄ -alkyl and

R₁ ", R₂ " and R₃ " have the abovementioned meaning;

and ##STR8## wherein R₁₀ ' represents phenyl and

R₁₁ ' represents methyl,

and wherein

R₁ ", R₂ " and R₃ " have the abovementioned meaning.

The dyestuffs of the formula (I) are known; their preparation is described in German Offenlegungsschrift (German Published Specification) No. 2,715,135 and German Patent Applications Nos. 27 52 424.9 and 28 51 575.5.

It has now been found that the dyestuffs of the formula (I), which are free from fibre-reactive groups, are outstandingly suitable for dyeing and printing cellulose fibres which can be swollen in water and fibre blends containing these fibres when they are applied by the process known from DE-AS (German Published Specification) No. 1,811,796. In this process, the fibres are brought into contact with an amount of water sufficient to swell the cellulose and with a water-miscible swelling agent before or at the same time as the treatment with the dyestuff. The swelling agent must be capable of maintaining the swelling of the cellulose when the water is removed and of dissolving the dyestuff at the dyeing temperature, if appropriate with the aid of an additional solubilising agent.

The swelling agent is in general added in an amount of 10 to 30% by weight, relative to the cellulose fibres. Suitable swelling agents have a boiling point above 150° C.

The dyestuff and swelling agent can be applied simultaneously to the fibre, or the fibre can be treated first with the swelling agent and then with the aqueous dyestuff dispersion.

Finally, the dyestuff is fixed by heat treatment, in particular at 150°-230° C.

The process is suitable for dyeing and printing both natural cellulose and regenerated cellulose.

The process is of particular interest for dyeing and printing fibre blends of cellulose and synthetic fibres, such as polyamide and polyester fibres, in particular cotton/polyester fibre blends, since it makes matching shade dyeing or printing in a single procedure possible.

Processes of this type and further auxiliaries which can be used instead of the products known from DE-AS (German Published Specification) No. 1,811,796 are known, for example, from German Offenlegungsschriften (German Published Specifications) Nos. 2,524,243, 2,528,743 and 2,751,830.

The dyestuffs (I) give dyeings and prints, the colour shades of which are between yellow and red and match well on the fibre blends. They are distinguished by very good fastness properties, and in addition to fastness to washing, fastness to sublimation, light and dry cleaning should above all be singled out.

The dyestuff formulations according to the invention can contain, in addition to water, customary constituents, such as dispersing agents, for example non-ionic and/or anionic and/or cationic dispersing agents, thickeners and/or swelling agents and/or dyestuff solubilising agents.

The parts mentioned in the examples below are parts by weight and the degrees are degrees Centigrade.

EXAMPLE 1

(a) 50-200 parts of the dyestuff of the formula ##STR9## are brought together with 25 to 100 parts of a non-ionic dispersing agent, the mixture is made up to 1,000 parts with water and dispersion is then effected in a ball mill or another suitable apparatus. In order to prevent the dyestuff paste from drying out too rapidly, a small amount of preservative and glycols or glycerol can also be added to the paste.

(b) A PES/CO 50:50 fabric is printed with a printing paste consisting of

    ______________________________________                                         1- 50 parts of the dyestuff paste from paragraph a)                            100 parts   of polyethylene glycol (molecular weight:                                      about 400)                                                         399- 350 parts                                                                             of water and                                                       500 parts   of a 10% strength guar flour thickener                             1,000 parts                                                                    ______________________________________                                    

using a rotary screen printing machine or screen printing tables. (If a roller printing machine is used, the amount of polyethylene glycol must be increased to 150-200 parts, depending on the depth of the gravure cells.)

The fabric is then dried, the dyestuff is fixed at 210° with dry heat for 1 minute and the fabric is rinsed, soaped, rinsed again and dried.

A scarlet-red print which is fast to washing and fast to light is obtained.

EXAMPLES 2-32

The procedure followed is as described in Example 1, but the dyestuffs of the formula ##STR10## described in the following table are used.

    __________________________________________________________________________                                                              Colour                Ex.                                                                               R.sub.1    R.sub.2                                                                            R.sub.3                                                                            R.sub.4      R.sub.5    R.sub.6    shade                 __________________________________________________________________________     2  C.sub.6 H.sub.5                                                                           NO.sub.2                                                                           H   NHCOCH.sub.3 C.sub.2 H.sub.4 OCOC.sub.6 H.sub.5                                                        C.sub.2 H.sub.4 OCOC.sub.6                                                     H.sub.5    red                   3  3-ClC.sub.6 H.sub.4                                                                       Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 OCOOC.sub.2                                                    H.sub.5    scarlet               4  3-CH.sub.3C.sub.6 H.sub.4                                                                 Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OCOOCH.sub.3                                                              C.sub.2 H.sub.4 OCOOCH.sub.3                                                              "                     5  3-CH.sub.3C.sub.6 H.sub.4                                                                 Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 OCOOC.sub.2                                                    H.sub.5    "                     6  C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOC.sub.4 H.sub.9                                                                         C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                               "                     7  2-CH.sub.3C.sub.6 H.sub.4                                                                 Cl  Cl  NHCOC.sub.6 H.sub.5                                                                         C.sub.2 H.sub.4 OCOC.sub.2 H.sub.5                                                        C.sub.2 H.sub.4 OCOC.sub. 2                                                    H.sub.5    "                     8  4-ClC.sub.6 H.sub.4                                                                       Cl  Cl  NHSO.sub.2 CH.sub.3                                                                         C.sub.2 H.sub.4 OCONHCH.sub.3                                                             C.sub.2 H.sub.4 OCONHCH.sub.                                                   3          "                     9  3-ClC.sub.6 H.sub.4                                                                       Cl  Cl  NHSO.sub.2 C.sub.4 H.sub.9                                                                  C.sub.2 H.sub.4 OCOOCH.sub.3                                                              C.sub.2 H.sub.4 OCOOCH.sub.3                                                   .          "                     10 C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OCONHC.sub.4 H.sub.9                                                      C.sub.2 H.sub.4 OCONHC.sub.4                                                    H.sub.9   "                     11 3-CH.sub.3C.sub.6 H.sub.4                                                                 Cl  Cl  NHCOC.sub.3 H.sub.7                                                                         C.sub.2 H.sub.4 OCOC.sub.6 H.sub.5                                                        C.sub.2 H.sub.4 OCOC.sub.6                                                     H.sub.5    "                     12 C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 CN                                                                        C.sub.2 H.sub.4 OCONHC.sub.6                                                    H.sub.5   "                     13 3-ClC.sub.6 H.sub.4                                                                       Cl  Cl  NHSO.sub.2 C.sub.6 H.sub.5                                                                  C.sub.2 H.sub.4 OCOOCH.sub.3                                                              C.sub.2 H.sub.4 OCOOCH.sub.3                                                              "                     14 3,5-CH.sub.3C.sub.6 H.sub.3                                                               CH.sub.3                                                                           CH.sub.3                                                                           NHSO.sub.2(4-CH.sub.3)C.sub.6 H.sub.4                                                       C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.                                                     3          "                     15 C.sub.6 H.sub.5                                                                           CF.sub.3                                                                           Cl  NHCONH.sub.2 C.sub.2 H.sub.4 CN                                                                        C.sub.2 H.sub.4 OCOOC.sub.2                                                    H.sub.5    "                     16 3-CH.sub.3C.sub.6 H.sub.4                                                                 Br  Br  OSO.sub.2 C.sub.6 H.sub.5                                                                   C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 OCOOC.sub.2                                                    H.sub.5    "                     17 C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOOCH.sub.3                                                                               C.sub.2 H.sub.4 COOCH.sub.3                                                               C.sub.2 H.sub.4 COOCH.sub.3                                                               "                     18 C.sub.6 H.sub.5                                                                           CN  Br  NHCONHC.sub.6 H.sub.5                                                                        ##STR11##                                                                                 ##STR12## red                   19 3,5-CH.sub.3 -4-ClC.sub.6 H.sub.2                                                         Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                               scarlet               20 C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOCF.sub.3 C.sub.2 H.sub.4 OCOOC.sub.2 H.sub.5                                                       C.sub.2 H.sub.4 OCOOC.sub.2                                                    H.sub.5    scarlet               21 3-ClC.sub.6 H.sub.4                                                                       NO.sub.2                                                                           Cl  NHSO.sub.2 C.sub.4 H.sub.9                                                                  C.sub.2 H.sub.4 CN                                                                        C.sub.2 H.sub.4 OCOC.sub.6                                                     H.sub.5    red                   22 C.sub.6 H.sub.5                                                                           OCH.sub.3                                                                          OCH.sub.3                                                                          OSO.sub.2 CH.sub.3                                                                          C.sub.2 H.sub.4 OCOOCH.sub.3                                                              C.sub.2 H.sub.4 OCOOCH.sub.3                                                              red                   23 3-CH.sub.3C.sub.6 H.sub.4                                                                 CN  CN  NHCOCH.sub.3 C.sub.2 H.sub.4 OSO.sub.2 C.sub.6                                              H.sub.5    C.sub.2 H.sub.4 OSO.sub.2                                                      C.sub.6 H.sub.5                                                                           red                   24 4-CH.sub.3C.sub.6 H.sub.4                                                                 CF.sub.3                                                                           CF.sub.3                                                                           NHCOCH.sub.3 C.sub.2 H.sub.4 OCOCH.sub.3                                                               C.sub.2 H.sub.4 OCOCH.sub.3                                                               scarlet               25 C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OSO.sub.2 CH.sub.3                                                        C.sub.2 H.sub.4 OSO.sub.2                                                      CH.sub.3   scarlet               26 3-ClC.sub.6 H.sub.4                                                                       Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OSO.sub.2 C.sub.4                                              H.sub.9    C.sub.2 H.sub.4 OSO.sub.2                                                      C.sub.4 H.sub.9                                                                           scarlet               27 C.sub.6 H.sub.5                                                                           Cl  Cl  NHCOCH.sub.3 H          C.sub.2 H.sub.5                                                                           scarlet               28 3-NO.sub.2C.sub.6 H.sub.4                                                                 Cl  Cl  H            C.sub.2 H.sub.5                                                                           CH.sub.2 C.sub.6 H.sub.5                                                                  orange                29 C.sub.6 H.sub.5                                                                           Cl  Cl  CH.sub.3     C.sub.2 H.sub.4 OCH.sub.3                                                                 C.sub.2 H.sub.4 OCH.sub.3                                                                 yellowish-                                                                     tinged                                                                         scarlet               30 C.sub.6 H.sub.5                                                                           Cl  Cl  OCH.sub.3    C.sub.2 H.sub.5                                                                           C.sub.2 H.sub.5                                                                           yellowish-                                                                     tinged                                                                         scarlet               31 C.sub.6 H.sub.5                                                                           Cl  Cl  Cl           CH.sub.2CHCH.sub.2                                                                        CH.sub.2CHCH.sub.2                                                                        orange-                                                                        brown                 32 3-ClC.sub.6 H.sub.4                                                                       Cl  Cl  NHCOCH.sub.3 C.sub.2 H.sub.4 OCOOCH.sub.3                                                              C.sub.2 H.sub.4 OCOOCH.sub.3                                                              scarlet               __________________________________________________________________________

EXAMPLES 33-53

The procedure followed is as indicated in Example 1, but the dyestuffs of the formula ##STR13## described in the table below are used.

    __________________________________________________________________________     Example                                                                             R.sub.1  R.sub.2                                                                            R.sub.3                                                                            R.sub.7                                                                               R.sub.8  R.sub.9                                                                            Colour shade                         __________________________________________________________________________     33   3-ClC.sub.6 H.sub.4                                                                     Cl  Cl  C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               34   C.sub.6 H.sub.5                                                                         Cl  Cl  C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               35   3-CH.sub.3C.sub.6 H.sub.4                                                               Cl  Cl  C.sub.6 H.sub.5                                                                       C.sub.2 H.sub.5                                                                         H   orange                               36   C.sub.6 H.sub.5                                                                         NO.sub.2                                                                           H   C.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4 OH                                                                      H   orange                               37   3,5-CH.sub.3C.sub.6 H.sub.3                                                             CH.sub.3                                                                           CH.sub.3                                                                           C.sub.6 H.sub.5                                                                        ##STR14##                                                                              H   orange                               38   3-NO.sub.2C.sub.6 H.sub.4                                                               CF.sub.3                                                                           Cl  C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               39   C.sub.6 H.sub.5                                                                         Br  Br  C.sub.6 H.sub.5                                                                       C.sub.4 H.sub.9                                                                         H   orange                               40   3-ClC.sub.6 H.sub.4                                                                     CN  Br  C.sub.2 H.sub.5                                                                       CH.sub.3 H   golden yellow                        41   3-CH.sub.3C.sub.6 H.sub.4                                                               NO.sub.2                                                                           Cl  CH.sub.3                                                                              CH.sub.3 H   golden yellow                        42   C.sub.6 H.sub.5                                                                         OCH.sub.3                                                                          OCH.sub.3                                                                          C.sub.4 H.sub.9                                                                       CH.sub.3 H   gplden yellow                        43   C.sub.6 H.sub.5                                                                         CN  CN  C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               44   3-ClC.sub.6 H.sub.4                                                                     CF.sub.3                                                                           CF.sub.3                                                                           C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               45   3-ClC.sub.6 H.sub.4                                                                     Cl  H   C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               46   C.sub.6 H.sub.5                                                                         NO.sub.2                                                                           H   C.sub.6 H.sub.5                                                                       CH.sub.3 H   orange                               47   3-ClC.sub.6 H.sub.4                                                                     Cl  Cl  C.sub.6 H.sub.5                                                                       H        H   orange                               48   C.sub.6 H.sub.5                                                                         Cl  Cl  CH.sub.3                                                                              CH.sub.2C.sub.6 H.sub.5                                                                 H   golden yellow                        49   C.sub.6 H.sub.5                                                                         Cl  Cl  C.sub.6 H.sub.5                                                                       C.sub.2 H.sub.4C.sub.6 H.sub.5                                                          H   orange                               50   3-CH.sub.3C.sub.6 H.sub.4                                                               Cl  Cl  C.sub.6 H.sub.5                                                                       CH.sub.3 7-C.sub.2 H.sub.5                                                                  orange                               51   C.sub.6 H.sub.5                                                                         Cl  Cl  C.sub.6 H.sub.5                                                                       CH.sub.3 5-Cl                                                                               orange                               52   C.sub.6 H.sub.5                                                                         Cl  Cl  4-CH.sub.3C.sub.6 H.sub.4                                                             CH.sub.3 H   orange                               53   C.sub.6 H.sub.5                                                                         Cl  Cl  C.sub.6 H.sub. 5                                                                      C.sub.4 H.sub.9                                                                         H   orange                               __________________________________________________________________________

EXAMPLES 54-69

The procedure followed is as indicated in Example 1, but the dyestuffs of the formula ##STR15## described in the table below are used.

    __________________________________________________________________________     Example                                                                             R.sub.1 R.sub.2                                                                            R.sub.3                                                                            R.sub.10  R.sub.11                                                                             Colour shade                              __________________________________________________________________________     54   3-CH.sub.3C.sub.6 H.sub.4                                                              Cl  Cl  C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    55   C.sub.6 H.sub.5                                                                        Cl  Cl  C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    56   3-ClC.sub.6 H.sub.4                                                                    Cl  Cl  C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    57   C.sub.6 H.sub.5                                                                        NO.sub.2                                                                           H   C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    58   3-CH.sub.3C.sub.6 H.sub.4                                                              CH.sub.3                                                                           CH.sub.3                                                                           2-ClC.sub.6 H.sub.4                                                                      CH.sub.3                                                                             yellow                                    59   C.sub.6 H.sub.5                                                                        CF.sub.3                                                                           Cl  CH.sub.2C.sub.6 H.sub.5                                                                  CH.sub.3                                                                             yellow                                    60   C.sub.6 H.sub.5                                                                        Br  Br  C.sub.4 H.sub.9                                                                          CH.sub.3                                                                             yellow                                    61   3-NO.sub.2C.sub.6 H.sub.4                                                              Cl  Cl                                                                                  ##STR16##                                                                               CH.sub.3                                                                             yellow                                    62   C.sub.6 H.sub.5                                                                        CN  Br  3-NO.sub.2C.sub.6 H.sub.4                                                                CH.sub.3                                                                             yellow                                    63   3-CH.sub.3C.sub.6 H.sub.4                                                              NO.sub.2                                                                           Cl  2,5-ClC.sub.6 H.sub.3                                                                    CH.sub.3                                                                             yellow                                    64   C.sub.6 H.sub.5                                                                        OCH.sub.3                                                                          OCH.sub.3                                                                          C.sub.6 H.sub.5                                                                          COOC.sub.2 H.sub.5                                                                   yellow                                    65   C.sub.6 H.sub.5                                                                        CN  CN  C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    66   3-ClC.sub.6 H.sub.4                                                                    CF.sub.3                                                                           CF.sub.3                                                                           C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    67   3-ClC.sub.6 H.sub.4                                                                    Cl  H   4-CH.sub.3C.sub.6 H.sub.4                                                                CH.sub.3                                                                             yellow                                    68   3,5-CH.sub.3C.sub.6 H.sub.3                                                            Cl  Cl  C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    69   3-CH.sub.3C.sub.6 H.sub.4                                                              NO.sub.2                                                                           H   C.sub.6 H.sub.5                                                                          CH.sub.3                                                                             yellow                                    __________________________________________________________________________

EXAMPLE 70

(a) 50-200 parts of the dyestuff of the formula ##STR17## are brought together with 25 to 100 parts of a non-ionic dispersing agent, the mixture is made up to 1,000 parts with water and dispersion is effected in a ball mill or another apparatus. In order to prevent the dyestuff paste from drying out too rapidly, a small amount of preservative and glycols or glycerol can also be added to the paste.

(b) A PES/CO 65:35 fabric is printed with a printing paste consisting of

    ______________________________________                                         1- 50 parts                                                                              of the dyestuff paste from paragraph a)                              100 parts of the boric acid ester of polyethylene glycol                                 (molecular weight: 300)                                              399- 350 parts                                                                           of water and                                                         500 parts of a 4% strength alginate thickener                                  1,000 parts                                                                    ______________________________________                                    

using a rotary screen printing machine or screen printing tables.

An orange print which is fast to washing and light is obtained. 

We claim:
 1. Process for dyeing and printing cellulose fibres swollen with water-miscible swelling agents or fibre blends containing these fibres, characterised in that the fibres are treated with dyestuffs of the general formula ##STR18## wherein R₁ represents aryl,R₂ represents halogen, CN, CF₃, NO₂, Q₁, --OQ₁, --COOQ₁, --CONQ₁ Q₂ or --NHCOQ₁, R₃ represents H, halogen, CN, CF₃, Q₁ or --OQ₁ and K represents the radical of a coupling component,wherein Q₁ denotes alkyl or aryl and Q₂ denotes hydrogen, alkyl or aralkyl,and the dyestuffs are fixed by heat treatment.
 2. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula of claim 1 wherein K represents the radical of an aniline coupling component which couples in the 4-position, the radical of an indole coupling component which couples in the 3-position or the radical of a 5-aminopyrazole coupling component which couples in the 4-position.
 3. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula ##STR19## wherein R₁ ' represents phenyl, which is optionally mono-, di- or tri-substituted by C₁ -C₄ -alkyl or halogen,R₂ ' represents halogen, CN, CF₃, NO₂, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, R₃ ' represents halogen, CN, CF₃, C₁ -C₄ -alkyl or C₁ -C₄ -alkoxy, R₄ represents hydrogen, halogen, alkyl, --NHCOQ₁, --NHSO₂ Q₁, --NHCONH₂, --NHCONQ₁ Q₂, --NHCOCF₃, --NHCOOQ₁, alkoxy or --O--SO₂ --Q₁, R₅ and R₆, which can be identical or different, represent hydrogen, C₁ -C₄ -alkyl, --C₁ -C₄ -alkylene--O--CO--Q₁, C₁ -C₄ -alkylene--O--CO--O--Q₁, C₁ -C₄ -alkylene--CO--O--Q₁, C₁ -C₄ -alkylene--CONQ₁ Q₂, C₁ -C₄ -alkylene--O--Q₁, C₁ -C₄ -alkylene--O--CO--NH--Q₁, C₁ -C₄ -alkylene--O--SO₂ -Q₁, aralkyl, --CH₂ --CH═CH₂ or --CH₂ CH₂ CN and Q₁ and Q₂ have the abovementioned meaning,and the dyestuffs are fixed by heat treatment,
 4. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula ##STR20## wherein R₇ represents C₁ -C₄ -alkyl or phenyl,R₈ represents C₁ -C₄ -alkyl, benzyl or phenethyl, R₉ represents hydrogen, halogen or alkyl and R₁ ', R₂ ' and R₃ 'have the abovementioned meaning,and the dyestuffs are fixed by heat treatment.
 5. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula ##STR21## wherein R₁₀ represents Q₂, aryl, cycloalkyl or the radical of a heterocyclic compound andR₁₁ represents Q₁, --COOQ₂ or --CON(Q₂)₂,and wherein R₁ ', R₂ ', R₃ ', Q₁ and Q₂ have the abovementioned meaning,and the dyestuffs are fixed by heat treatment.
 6. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula ##STR22## wherein R₁ " represents phenyl, tolyl or chlorophenyl,R₂ " represents halogen, nitro or cyano, R₃ " represents halogen, R₄ ' represents --NHCOCH₃, --NHCOC₂ H₅, --NHCOC₃ H₇, --NHCOC₄ H₉, --NHCOC₆ H₅ or --NHSO₂ CH₃, --NHSO₂ C₄ H₉ or --NHSO₂ C₆ H₅ and R₅ ' and R₆ ', which can be identical or different, represent --C₂ H₄ --O--CO--CH₃, --C₂ H₄ --O--COC₂ H₅, --C₂ H₄ --O--CO--C₆ H₅, --C₂ H₄ --O--CO--O--CH₃, --C₂ H₄ --O--CO--O--C₂ H₅, --C₂ H₄ --O--CO--NH--CH₃, --C₂ H₄ --O--CO--NH--C₄ H₉, --C₂ H₄ --O--CO--NH--C₆ H₅ or --C₂ H₄ CN,and the dyestuffs are fixed by heat treatment.
 7. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula ##STR23## wherein R₇ ' represents phenyl,R₈ ' represents C₁ -C₄ -alkyl and R₁ ", R₂ " and R₃ "have the abovementioned meaning,and the dyestuffs are fixed by heat treatment.
 8. Process according to claim 1, characterised in that the fibres are treated with dyestuffs of the formula ##STR24## wherein R₁₀ ' represents phenyl andR₁₁ ' represents methyl,and wherein R₁ ", R₂ " and R₃ " have the abovementioned meaning,and the dyestuffs are fixed by heat treatment.
 9. Formulation for dyeing and printing cellulose fibres swollen with water-miscible swelling agents or fibre blends containing these fibres, characterised in that it cotains one or more dyestuffs of the formula of claim
 1. 